Divergent Reactivity in Pd-Catalyzed [3,3]-Sigmatropic Rearrangement of Allyloxy- and Propargyloxyindoles Revealed by Computation and Experiment. Academic Article

abstract

• Detailed computational (DFT) studies of the palladium(II)-catalyzed Claisen rearrangement of 2-allyloxy- and propargyloxyindoles revealed an unexpected divergent mode of reactivity. Subsequent experimental kinetic isotope effects are in accord with the mechanism derived from the computations. The computational results led to the development of Pd(II)-catalyzed [3,3]-sigmatropic rearrangement of 3-aryl substituted 2-propargylindoles.

authors

• Gutierrez Santacruz, Osvaldo

published proceedings

• Org Lett

author list (cited authors)

• Gutierrez, O., Hendrick, C. E., & Kozlowski, M. C.

citation count

• 10

complete list of authors

• Gutierrez, Osvaldo||Hendrick, Charles E||Kozlowski, Marisa C

publication date

• October 2018

publisher

• American Chemical Society (ACS)  Publisher

published in

• Organic Letters  Journal

keywords

• Carbon Isotopes
• Catalysis
• Indoles
• Kinetics
• Models, Chemical
• Palladium
• Thermodynamics

PubMed Central ID

• 30295492

Digital Object Identifier (DOI)

• 10.1021/acs.orglett.8b02864

start page

• 6539

end page

• 6543

volume

• 20

issue

• 20

URL

• http://dx.doi.org/10.1021/acs.orglett.8b02864